含查尔酮结构香豆素衍生物的合成及抗肿瘤增殖活性
Synthesis and antitumor activities of novel coumarin derivatives containing chalcone moiety
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摘要: 基于活性亚单元拼接原理,将查尔酮分子片段拼接到香豆素结构中,设计并合成了一系列新型含查尔酮结构的香豆素衍生物;以苯乙酮和对甲基苯甲醛为原料,经克莱森-施密特缩合、溴代、环合、消除等反应制备得到24个目标化合物;化合物结构经1H NMR、ESI-MS确证。采用MTT法评价了化合物对HepG2、DU145及A549肿瘤细胞的抗增殖作用。结果表明,部分化合物对肿瘤细胞具有较好抗增殖作用,其中 Ⅰc , Ⅱb , Ⅱc和Ⅱd 对HepG2和A549的抗增殖作用较强,IC50分别为2.05~9.16 mol/L和3.48~10.81 mol/L,在此基础上初步探讨了此类化合物的构效关系。Abstract: To explore novel coumarin derivatives with more potent antitumor activity, a series of novel compounds were designed and synthesized by linking chalcone to coumarin′s framework. Starting from acetophenone and 4-methylbenzaldehyde, the target compounds were prepared through a reaction cascade, including Claisen-Schmidt, bromination, cyclization and elimination reactions affording twenty-four novel compounds whose structures were confirmed by 1H NMR and ESI-MS techniques. In vitro antitumor activities of the compounds were evaluated against HepG2, DU145 and A549 cell lines by the standard MTT assay. The results showed that some of the target compounds exhibited strong anti-proliferative activities against selected tumor cells. Compounds Ⅰc, Ⅱb, Ⅱc and Ⅱd showed excellent anti-proliferative activities against HepG2 and A549 cell lines with the IC50 values of 2. 05-9. 16 mol/L and 3. 48-10. 81 mol/L, respectively. The structure-activity relationship of novel coumarin derivatives containing chalcone moiety is also discussed.
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Keywords:
- coumarin /
- chalcone /
- molecular hybridization /
- synthesis /
- antitumor
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草珊瑚(Sarcandra glabra)为金粟兰科(Chloranthaceae)草珊瑚属植物,在我国主要分布于南部地区,具有清热凉血,活血消斑,祛风通络的功效,是用于治疗炎症性疾病、风湿关节痛的传统中药[1]。现代药理学研究表明,草珊瑚具有免疫调节[2]、抗炎[3]以及抗肿瘤[4]活性。近些年来,草珊瑚及其提取物在食品以及化妆品等行业的需求也在不断地增长[5]。本课题组围绕草珊瑚中的特征性成分进行了诸多探索[6−7]。乌药烷倍半萜及其聚合物以其独特的3/5/6环结构、多样的聚合方式以及良好的生物活性也被认为是草珊瑚中最有代表性的化合物[8−9]。目前对于草珊瑚的化学成分的研究主要集中于极性较小的萜类成分,对于草珊瑚提取物中的大极性成分,特别是苷类成分研究较少[10]。
为了阐明草珊瑚作为常用中药的物质基础,进一步深入研究其中的有效成分。本研究对新鲜草珊瑚叶醇提物乙酸乙酯萃取后水部位进行了系统的研究。从中分离鉴定了8个极性较大的萜苷类化合物和2个迷迭香酸衍生物,分别为sarcaglaboside C (1)、sarcaglaboside D (2)、byzantionoside B (3)、lauroside E (4)、(4Z)-4-[(3S)-3-(β-D-glucopyranosyloxy)butylidene]-3,5,5-trimethyl-2-cyclohexen-1-one (5)、dihydrovomifoliol-O-β-D-glucopyranoside (6)、(+)-abscisyl-β-D-glucopyranoside (7)、9ξ-O-β-D-glucopyranosyloxy-5-megastigmen-4-one (8)、rosmarinic acid methyl ester (9)、methyl isorinate (10)。其中,化合物3~5,8~9均首次从草珊瑚中分离得到。
1. 仪器与材料
1.1 药 材
草珊瑚地上部分(约51.5 kg)采自福建省三明市,由中国药科大学生药学教研室张勉教授鉴定为金粟兰科草珊瑚属草珊瑚[Sarcandra glabra (Thunb.) Nakai],凭证标本(202106)存放于中国药科大学中药学院天然药物化学教研室。
1.2 仪器与试剂
1260/1100分析型高效液相色谱仪、G6520B Q-TOF质谱仪(美国安捷伦公司);制备型高效液相色谱仪、紫外光谱仪(日本岛津公司);AV-600型核磁共振仪(美国布鲁克公司);200~300目硅胶,GF254硅胶(青岛海洋化工有限公司);MCI树脂(三菱化学公司);RP-C18反相柱色谱填料(上海月旭科技公司);Sephadex LH-20(英国GE healthcare Bio-Sciences AB公司);氘代试剂(美国剑桥同位素实验室);所用试剂均为分析纯或色谱纯。
2. 提取与分离
新鲜的草珊瑚地上部分(51.5 kg),粉碎,用3倍量的85%乙醇回流提取3次,每次3 h。提取液减压浓缩后得到粗浸膏(
1553 g)。取适量水使之混悬,依次用2倍量的乙酸乙酯进行萃取,分别得到水部位(731.2 g)和乙酸乙酯部位(545.3 g)。水部位分别经大孔树脂柱色谱粗分段,用乙醇-水(0︰1→1︰0)梯度洗脱,得到5个馏分(Fr. A-E)。对馏分Fr. B以及Fr. C采用硅胶柱色谱、MCI柱色谱、凝胶柱色谱、制备液相色谱等分离方法,共得到10个化合物。其中,在馏分Fr. B中分离得到化合物1,5~10,在馏分Fr. B中分离得到化合物2~4。化合物1~10 的结构式见图1。3. 结 果
化合物1 白色无定形粉末,(+)-HR-ESI-MS m/z
433.1851 [M+Na]+。分子式为C21H30O8。其1H NMR谱图显示了1组葡萄糖基信号,2个甲基单峰信号;5个烯氢信号;1个连氧取代氢信号。13C NMR谱图显示1个酯羰基碳信号,3组碳碳双键信号,1个缩醛碳信号。结合以上信息分析该化合物为榄香烷倍半萜糖苷类化合物。具体的核磁数据如下:1H NMR (600 MHz, MeOD) δ: 5.83 (1H, m, H-1), 4.99 (1H, m, H-2α), 5.01 (1H, m, H-2β), 5.06 (1H, m, H-3α), 5.40 (1H, m, H-3β), 2.34 (1H, dd, J=12.2 Hz, 3.2 Hz, H-5), 2.81 (1H, dd, J=14.4 Hz, 4.2Hz, H-6α), 2.72 (1H, t, J=13.9 Hz, H-6β), 4.92 (1H, m, H-8), 1.36 (1H, t, J=12 Hz, H-9α), 2.14 (1H, dd, J =12.1 Hz, 6.1Hz, H-9β), 1.80 (1H, s, H3-13), 1.21 (1H, s, H3-14), 4.08 (1H, d, J=13 Hz, H-15α), 4.29 (1H, d, J=13 Hz, H-15β), 4.25 (1H, d, J=7.8 Hz, H-1′), 3.34 (1H, t, J=8.9 Hz, H-2′), 3.27 (1H, d, J=8.7 Hz, H-3′), 3.24 (1H, ddd, J=9.6Hz, 5.7Hz, 2.2Hz, H-4′), 3.20 (1H, dd, J=9.2 Hz, 7.9 Hz, H-5′), 3.66 (1H, dd, J=11.9 Hz, 5.5 Hz, H-6′α), 3.86 (1H, dd, J=11.8 Hz, 2.3 Hz, H-6′β); 13C NMR (150 MHz, MeOD) δ: 146.7 (C-1), 111.2 (C-2), 119.0 (C-3), 145.9 (C-4), 55.8 (C-5), 27.9 (C-6), 163.8 (C-7), 78.4 (C-8), 45.6 (C-9), 40.6 (C-10), 119.2 (C-11), 176.0 (C-12), 6.7 (C-13), 15.3 (C-14), 73.3 (C-15), 102.9 (C-1′), 73.8 (C-2′), 76.8 (C-3′), 70.3 (C-4′), 76.6 (C-5′), 61.4 (C-6′)。该化合物的波谱数据与文献[11]报道的基本一致,故鉴定化合物1为sarcaglaboside C。化合物2 白色无定形粉末,(+)-HR-ESI-MS m/z
565.2284 [M+Na]+。分子式为C26H38O12。1H NMR (600 MHz, MeOD) δ: 5.84 (1H, m, H-1), 5.02 (1H, m, H-2α), 5.02 (1H, m, H-2β), 5.02 (1H, m, H-3α), 5.42 (1H, m, H-3β), 2.73 (1H, t, J=13.9 Hz, H-5), 2.86 (1H, dd, J=14.4 Hz, 4.1 Hz, H-6α), 2.34 (1H, dd, J=13.4 Hz, 4 Hz, H-6β), 4.92 (1H, m, H-8), 1.38 (1H, t, J=12 Hz, H-9α), 2.16 (1H, dt, J=13.5 Hz, 6.7 Hz, H-9β), 1.82 (1H, s, H3-13), 1.23 (1H, s, H3-14), 4.10 (1H, d, J=12.9 Hz, H-15α), 4.26 (1H, m, H-15β), 4.27 (1H, m, H-1′), 3.21 (1H, m, H-2′), 3.37 (1H, m, H-3′), 3.27 (1H, t, J=9.3 Hz, H-4′), 3.37 (1H, m, H-5′), 3.40 (1H, m, H-6′α), 3,96 (1H, m, H-6′β), 4.93 (1H, m, H-1′′), 3.78 (1H, d, J=9.5 Hz, H-2′′), 3.61 (1H, dd, J=11.3 Hz, 6.5 Hz, H-4′′α), 3.91 (1H, d, J=2.5 Hz, H-4′′β), 3.59 (1H, br.s, H-5′′α), 3.59 (1H, br.s, H-5′′β); 13C NMR (150 MHz, MeOD) δ: 147.3 (C-1), 111.8 (C-2), 114.7 (C-3), 146.3 (C-4), 54.4 (C-5), 28.4 (C-6), 164.5 (C-7), 79.7 (C-8), 46.2 (C-9), 41.2 (C-10), 119.7 (C-11), 176.5 (C-12), 7.3 (C-13), 15.9 (C-14), 74.3 (C-15), 103.5 (C-1′), 74.1 (C-2′), 77.2 (C-3′), 70.9 (C-4′), 76.2 (C-5′), 67.9 (C-6′), 110.1 (C-1′′), 77.2 (C-2′′), 79.0 (C-3′′), 74.1 (C-4′′), 64.6 (C-5′′)。该化合物的波谱数据与文献[11]报道的基本一致,故鉴定化合物2为sarcaglaboside D。化合物3 黄色油状物,(+)-HR-ESI-MS m/z
395.2214 [M+Na]+。分子式为C19H32O7。其1H NMR谱图显示了1组葡萄糖基信号,3个甲基单峰信号;1个甲基双峰信号,1个烯氢信号,1个连氧取代氢信号。13C NMR谱图显示1个酮羰基碳信号,1组碳碳双键信号,1个缩醛碳信号。结合以上信息分析该化合物为紫罗兰酮型倍半萜糖苷类化合物。具体的核磁数据如下:1H NMR (600 MHz, MeOD) δ: 1.98 (1H, m, H-2α), 2.46 (1H, d, J=17.4 Hz, H-2β), 5.81 (1H, s, H-4), 1.98 (1H, m, H-6), 1.50 (1H, ddd, J=19.2 Hz, 9.6 Hz, 4.8 Hz, H-7α), 1.98 (1H, m, H-7β), 1.65 (1H, m, H-8α), 1.65 (1H, m, H-8β), 3.91 (1H, m, H-9), 1.19 (1H, d, J=6.2 Hz, H-10), 1.00 (1H, s, H3-11), 1.09 (1H, s, H3-12), 2.05 (1H, s, H3-13), 4.32 (1H, t, J=9.5 Hz, H-1′), 3.14 (1H, t, J=8.5 Hz, H-2′), 3.64 (1H, dt, J=15.1 Hz, 7 Hz, H-3′), 3.35 (1H, t, J=8.4 Hz, H-4′), 3.27 (1H, m, H-5′), 3.89 (1H, m, H-6′α), 3.83 (1H, m, H-6′β); 13C NMR (150 MHz, MeOD) δ: 46.7 (C-1), 36.6 (C-2), 201.0 (C-3), 124.0 (C-4), 168.7 (C-5), 51.0 (C-6), 36.4 (C-7), 35.9 (C-8), 70.5 (C-9), 23.6 (C-10), 25.4 (C-11), 26.1 (C-12), 18.5 (C-13), 100.7 (C-1′), 76.8 (C-2′), 73.8 (C-3′), 76.5 (C-4′), 74.2 (C-5′), 61.6 (C-6′)。该化合物的波谱数据与文献[12]报道的基本一致,故鉴定化合物3为byzantionoside B。化合物4 黄色油状物,(+)-HR-ESI-MS m/z
411.2116 [M+Na]+。分子式为C19H32O8。1H NMR (600 MHz, MeOD) δ: 2.05 (1H, m, H-2α), 2.46 (1H, d, J=17.4 Hz, H-2β), 5.81 (1H, s, H-4), 1.98 (1H, m, H-6), 1.50 (1H, m, H-7), 1.65 (1H, m, H-8α), 1.65 (1H, m, H-8β), 3.87 (1H, m, H-9), 1.19 (1H, d, J=6.2 Hz, H-10), 1.00 (1H, s, H3-11), 1.09 (1H, s, H3-12), 4.19 (1H, dd, J=15.6 Hz, 2 Hz, H-13), 4.36 (1H, dd, J=15.6 Hz, 2 Hz, H-13), 4.32 (1H, t, J=9.5 Hz, H-1′), 3.14 (1H, t, J=5.8 Hz, H-2′), 3.27 (1H, m, H-3′), 3.27 (1H, m, H-4′), 3.35 (1H, m, H-5′), 3.64 (1H, dp, J=15.1 Hz, 7 Hz, 6.4 Hz, H-6′α), 3.87 (1H, m, H-6′β); 13C NMR (150 MHz, MeOD) δ: 36.4 (C-1), 51.0 (C-2), 201.0 (C-3), 124.0 (C-4), 168.7 (C-5), 46.7 (C-6), 23.6 (C-7), 36.6 (C-8), 74.2 (C-9), 18.5 (C-10), 25.4 (C-11), 26.1 (C-12), 74.2 (C-13), 100.7 (C-1′), 73.8 (C-2′), 76.8 (C-3′), 70.5 (C-4′), 76.5 (C-5′), 61.5 (C-6′)。 该化合物的波谱数据与文献[13]报道的基本一致,故鉴定化合物4为lauroside E。化合物5 黄色油状物,(+)-HR-ESI-MS m/z
393.2136 [M+Na]+。分子式为C19H32O7。1H NMR (600 MHz, MeOD) δ: 2.66 (1H, dd, J=17.3 Hz, 11.6 Hz, 6.7 Hz, H-2α), 2.66 (1H, dd, J=17.3 Hz, 11.6 Hz, 6.7 Hz, H-2β), 5.86 (1H, s, H-4), 6.34 (1H, d, J=6.4 Hz, H-7), 2.31 (1H, d, J=8.6 Hz, H-8α), 2.31 (1H, d, J=8.6 Hz, H-8β), 4.35 (1H, d, J=7.8 Hz, H-9), 1.28 (1H, d, J=2.2 Hz, H-10), 1.25 (1H, s, H3-11), 1.25 (1H, s, H3-12), 2.11 (1H, s, H3-13), 4.36 (1H, m, H-1′), 4.03 (1H, m, H-2′), 3.26 (1H, dt, J=11.7 Hz, 6.5 Hz, H-3′), 3.15 (1H, m, H-4′), 3.35 (1H, m, H-5′), 3.84 (1H, m, H-6′α), 3.98 (1H, m, H-6′β); 13C NMR (150 MHz, MeOD) δ: 53.2 (C-1), 37.8 (C-2), 200.8 (C-3), 124.0 (C-4), 157.9 (C-5), 141.7 (C-6), 134.2 (C-7), 37.2 (C-8), 76.7 (C-9), 21.3 (C-10), 27.7 (C-11), 27.7 (C-12), 18.7 (C-13), 101.1 (C-1′), 73.7 (C-2′), 76.6 (C-3′), 70.5 (C-4′), 74.3 (C-5′), 61.7 (C-6′)。该化合物的波谱数据与文献[14]报道的基本一致,故鉴定化合物5为(4Z)-4-[(3S)-3-(β-D-glucopyranosyloxy)butylidene]-3,5,5-trimethyl-2-cyclohexen-1-one。化合物6 黄色油状物,(+)-HR-ESI-MS m/z
411.2116 [M+Na]+。分子式为C19H32O8。1H NMR (600 MHz, MeOD) δ: 2.61 (1H, d, J=12 Hz, H-2α), 2.15 (1H, d, J=12 Hz, H-2β), 5.83 (1H, s, H-4), 2.15 (1H, d, J=12 Hz, H-7α), 1.82 (1H, m, H-7β), 1.79 (1H, m, H-8α), 1.49 (1H, tt, J=12.9 Hz, 4.5 Hz, H-8β), 4.07 (1H, m, H-9), 1.17 (1H, d, J=6.2 Hz, H-10), 1.02 (1H, s, H3-11), 1.10 (1H, s, H3-12), 2.04 (1H, s, H3-13), 4.36 (1H, m, H-1′), 3.13 (1H, dd, J=9.2 Hz, 7.8 Hz, H-2′), 3.81 (1H, q, J=6 Hz, H-3′), 3.26 (1H, m, H-4′), 3.26 (1H, m, H-5′), 3.85 (1H, dd, J=11.6 Hz, 5.3 Hz, H-6′α), 3.34 (1H, m, H-6′β); 13C NMR (150 MHz, MeOD) δ: 42.0 (C-1), 50.2 (C-2), 200.2 (C-3), 125.8 (C-4), 170.9 (C-5), 78.4 (C-6), 34.0 (C-7), 32.7 (C-8), 75.3 (C-9), 20.9 (C-10), 23.8 (C-11), 23.3 (C-12), 19.2 (C-13), 101.4 (C-1′), 74.3 (C-2′), 77.0 (C-3′), 70.9 (C-4′), 77.3 (C-5′), 62.0 (C-6′)。该化合物的波谱数据与文献[15]报道的基本一致,故鉴定化合物6为dihydrovomifoliol-O-β-D-glucopyranoside。化合物7 黄色油状物,(+)-HR-ESI-MS m/z
459.1917 [M+Na]+。分子式为C21H30O9。1H NMR (600 MHz, MeOD) δ: 2.21 (1H, d, J=16.9 Hz, H-2α), 2.56 (1H, d, J=16.9 Hz, H-2β), 5.96 (1H, s, H-4), 6.35 (1H, d, J=16.1 Hz, H-7), 7.83 (1H, d, J=16.1 Hz, H-8), 5.84 (1H, s, H-10), 1.09 (1H, s, H3-12), 2.04 (1H, s, H3-13), 2.04 (1H, br.s, H3-14), 1.95 (1H, br.s, H3-15), 5.52 (1H, d, J=8.2 Hz, H-1′), 3.78 (1H, q, J=6.1 Hz, H-2′), 3.27 (1H, m, H-3′), 3.43 (1H, m, H-4′), 3.43 (1H, m, H-5′), 3.86 (1H, dd, J=12.1 Hz, 2.1 Hz, H-6′α), 3.71 (1H, m, H-6′β); 13C NMR (150 MHz, MeOD) δ: 41.5 (C-1), 49.2 (C-2), 199.5 (C-3), 126.3 (C-4), 152.2 (C-5), 77.4 (C-6), 137.9 (C-7), 127.8 (C-8), 128.5 (C-9), 116.7 (C-10), 164.4 (C-11), 18.1 (C-12), 18.1 (C-13), 22.2 (C-14), 19.9 (C-15), 94.0 (C-1′), 69.7 (C-2′), 76.7 (C-3′), 72.6 (C-4′), 67.8 (C-5′), 61.0 (C-6′)。该化合物的波谱数据与文献[16]报道的基本一致,故鉴定化合物7为 (+)-abscisyl-β-D-glucopyranoside。化合物8 黄色油状物,(+)-HR-ESI-MS m/z
395.2214 [M+Na]+。分子式为C19H32O7。1H NMR (600 MHz, MeOD) δ: 1.81 (1H, m, H-2α), 1.81 (1H, m, H-2β), 2.44 (1H, dd, J=7.5 Hz, 4.2 Hz, H-3α), 2.44 (1H, dd, J=7.5 Hz, 4.2 Hz, H-3β), 2.54 (1H, m, H-7α), 2.31 (1H, m, H-7β), 1.68 (1H, m, H-8α), 1.68 (1H, m, H-8β), 3.96 (1H, tt, J=7 Hz, 3.4 Hz, H-9), 1.76 (1H, s, H-10), 1.20 (1H, s, H3-11), 1.20 (1H, s, H3-12), 1.23 (1H, d, J=6.2 Hz, H-13), 4.35 (1H, d, J=7 Hz, H-1′), 3.16 (1H, m, H-2′), 3.28 (1H, m, H-3′), 3.31 (1H, m, H-4′), 3.28 (1H, m, H-5′), 3.88 (1H, ddd, J=11.4 Hz, 7 Hz, 1.4 Hz, H-6′α), 3.67 (1H, m, H-6′β); 13C NMR (150 MHz, MeOD) δ: 36.7 (C-1), 37.6 (C-2), 36.4 (C-3), 200.7 (C-4), 132.7 (C-5), 167.9 (C-6), 27.1 (C-7), 34.2 (C-8), 71.0 (C-9), 10.9 (C-10), 26.3 (C-11), 26.3 (C-12), 18.9 (C-13), 101.4 (C-1′), 74.9 (C-2′), 77.0 (C-3′), 74.3 (C-4′), 77.4 (C-5′), 62.1 (C-6′)。该化合物的波谱数据与文献[17]报道的基本一致,故鉴定化合物8为9ξ-O-β-D-glucopyranosyloxy-5-megastigmen-4-one。化合物9 白色方晶,(+)-HR-ESI-MS m/z
397.3121 [M+Na]+。分子式为C19H18O8。1H NMR (600 MHz, MeOD) δ: 7.05 (1H, d, J=2.1 Hz, H-2), 6.96 (1H, dd, J=8.2 Hz, 2 Hz, H-5), 6.78 (1H, d, J=8.1 Hz, H-6), 7.55 (1H, d, J=15.9 Hz, H-7), 6.26 (1H, d, J=15.9 Hz, H-8), 6.73 (2H, m, H-2′, H-6′), 6.57 (1H, dd, J=8.1 Hz, 2 Hz, H-5′), 3.04 (1H, qd, J=14.3 Hz, 6.4 Hz, H2-7′), 5.19 (1H, dd, J=7.7 Hz, 5.1 Hz, H-8′), 3.70 (1H, s, H3-OCH3); 13C NMR (150 MHz, MeOD) δ: 126.1 (C-1), 114.9 (C-2), 148.6 (C-3), 146.6 (C-4), 121.8 (C-5), 116.1 (C-6), 144.8 (C-7), 112.7 (C-8), 166.9 (C-9), 127.3 (C-1′), 115.1 (C-2′), 145.5 (C-3′), 144.8 (C-4′), 113.8 (C-5′), 120.4 (C-6′), 36.5 (C-7′), 73.3 (C-8′), 170.8 (C-9′), 51.3 (C-OCH3)。该化合物的波谱数据与文献[18]报道的基本一致,故鉴定化合物9为rosmarinic acid methyl ester。化合物10 白色方晶,(+)-HR-ESI-MS m/z
381.1117 [M+Na]+。分子式为C19H18O7。1H NMR (600 MHz, MeOD) δ: 7.06 (1H, d, J=2.1 Hz, H-2), 6.96 (1H, dd, J=8.2 Hz, 2 Hz, H-5), 6.81 (1H, d, J=8.1 Hz, H-6), 7.56 (1H, d, J=15.9 Hz, H-7), 6.27 (1H, d, J=15.9 Hz, H-8), 7.10 (2H, m, H-2′, H-6′), 6.75 (2H, dd, J=8.1 Hz, 2 Hz, H-3′, H-5′), 3.11 (1H, m, H2-7′), 5.22 (1H, dd, J=7.7 Hz, 5.1 Hz, H-8′), 3.71 (1H, s, H3-OCH3); 13C NMR (150 MHz, MeOD) δ: 126.2 (C-1), 113.9 (C-2), 148.6 (C-3), 146.6 (C-4), 121.8 (C-5), 112.7 (C-6), 156.0 (C-7), 122.3 (C-8), 166.9 (C-9), 130.1 (C-1′), 115.1 (C-2′, C-6′), 114.9 (C-3′, C-5′), 145.4 (C-4′), 36.3 (C-7′), 73.3 (C-8′), 170.8 (C-9′), 51.3 (C-OCH3)。该化合物的波谱数据与文献[19]报道的基本一致,故鉴定化合物10为methyl isorinate。4. 讨论与结论
草珊瑚中含有结构丰富的化合物,包括酚酸类,以乌药烷倍半萜及其多聚体组成的萜类,黄酮类以及香豆素类。本研究以草珊瑚地上部分的水萃取层为研究对象,系统地研究了其中的化学成分。从中发现了2个榄香烷糖苷类化合物,6个紫罗兰酮糖苷类化合物以及2个酚酸类化合物。上述化合物都具有较大的极性。其中,化合物3~5,8~9首次从草珊瑚中分离得到。这些化合物的发现有助于丰富草珊瑚植物中化合物的类型,有利于对草珊瑚作为常用中药含有的有效成分的理解,并为后续药理活性研究提供了重要的物质基础。基于草珊瑚用于治疗炎症性疾病的经验,后续可以对分离得到的上述化合物进行抗炎活性研究。
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